US9335644B2 - Electron transport material, electrophotographic photoreceptor, process cartridge, and image forming apparatus - Google Patents
Electron transport material, electrophotographic photoreceptor, process cartridge, and image forming apparatus Download PDFInfo
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- US9335644B2 US9335644B2 US14/617,263 US201514617263A US9335644B2 US 9335644 B2 US9335644 B2 US 9335644B2 US 201514617263 A US201514617263 A US 201514617263A US 9335644 B2 US9335644 B2 US 9335644B2
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Images
Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/10—Bases for charge-receiving or other layers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/41—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/86—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/94—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
-
- C07C2103/18—
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
Definitions
- the present invention relates to an electron transport material, an electrophotographic photoreceptor, a process cartridge, and an image forming apparatus.
- an electron transport material represented by the following formula (1):
- X represents an oxygen atom or ⁇ C(CN) 2
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 each independently represent a hydrogen atom, a halogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, an alkoxy group, an aryl group, or an aralkyl group
- R 8 , R 9 , and R 10 each independently represent a hydrogen atom, a halogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, an aralkyl group, an aryl group, —R 1 —O—R 12 , or —R 13 —CO—O—R 14
- R 11 represents a linear or branched alkylene group having 1 to 10 carbon atoms
- R 12 represents a linear or branched alkyl group having 1 to 10 carbon atoms
- R 13 represents a single bond or a linear
- FIG. 1 is a schematic partial cross-sectional view showing an electrophotographic photoreceptor according to the present exemplary embodiment
- FIG. 2 is a schematic structural view showing an image forming apparatus according to the present exemplary embodiment
- FIG. 3 is another schematic structural view showing an image forming apparatus according to the present exemplary embodiment
- FIG. 4 is a graph showing an infrared absorption spectrum of an exemplary compound (1-36) obtained in Synthesis Example 1;
- FIG. 5 is a graph showing an infrared absorption spectrum of an exemplary compound (1-37) obtained in Synthesis Example 2;
- FIG. 6 is a graph showing an infrared absorption spectrum of an exemplary compound (1-11) obtained in Synthesis Example 3;
- FIG. 7 is a graph showing an infrared absorption spectrum of an exemplary compound (1-12) obtained in Synthesis Example 4.
- FIG. 8 is a graph showing an infrared absorption spectrum of a comparative compound 1 obtained in Comparative Synthesis Example 1.
- the electron transport material according to the present exemplary embodiment is an electron transport material represented by the following formula (1).
- X represents an oxygen atom or ⁇ C(CN) 2 .
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 each independently represent a hydrogen atom, a halogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, an alkoxy group, an aryl group, or an aralkyl group.
- R 8 , R 9 , and R 10 each independently represent a hydrogen atom, a halogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, an aralkyl group, an aryl group, —R 11 —O—R 12 , or —R 13 —CO—O—R 4 .
- R 11 represents a linear or branched alkylene group having 1 to 10 carbon atoms.
- R 12 represents a linear or branched alkyl group having 1 to 10 carbon atoms.
- R 13 represents a single bond or a linear or branched alkylene group having 1 to 10 carbon atoms.
- R 14 represents a linear or branched alkyl group having 1 to 10 carbon atoms, an aryl group, or an aralkyl group, provided that at least two or more groups of R 8 , R 9 , and R 10 represent a group other than a hydrogen atom.
- a fluorenone derivative As a compound having a fluorenone skeleton (hereinafter referred to as a “fluorenone derivative” in some cases), there are many compounds having a high electron transport capability but have a low compatibility with a resin. Further, for example, a fluorenone derivative having an alkoxycarbonyl group introduced into a fluorenone skeleton as a substituent for improving the compatibility with a resin has a higher compatibility with a resin, as compared with the compound which does not have a substituent, but is susceptible to an effect by a stimulus from the outside (for example, heat, an electric field, and pressure).
- a stimulus from the outside for example, heat, an electric field, and pressure
- Examples of the effect by a stimulus from the outside include aggregation or diffusion of molecules of a fluorenone derivative in a system by a stimulus such as heat and pressure from the outside to a compound having a fluorenone derivative. Further, in the case where the molecules of a fluorenone derivative are easily aggregated or diffused in a system, it may be thought that depending on a stimulus such as heat and pressure from the outside, the distribution of fluorenone derivatives in a system is uneven.
- the electrophotographic photoreceptor using the electron transport material according to the present exemplary embodiment even when the image formation is repeated, blurring of an image due to a change in the film quality of the photosensitive layer or a change of the physical properties of the photosensitive layer surface hardly occurs.
- the film quality is hardly changed and the charge maintenance is good.
- the electron transport material according to the present exemplary embodiment has a phenyl group having two or more substituents incorporated thereinto, and therefore, it has a high melting point as well as high compatibility with a resin, as compared with a case where an electron transport material has a phenyl group having no substituent or a phenyl group having only one substituent incorporated thereinto.
- the electron transport material according to the present exemplary embodiment improvement of the compatibility with a resin and prevention of the morphological change of the film as well as an electron transport capability are accomplished. Further, by using an electrophotographic photoreceptor in which a resin layer including the electron transport material according to the present exemplary embodiment is used as a photosensitive layer, blurring of an image hardly occurs, and the charge maintenance becomes better.
- examples of the halogen atom represented by R 1 to R 7 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and from the viewpoints of the chemical stability, a fluorine atom and a chlorine atom are preferable.
- examples of the linear or branched alkyl group having 1 to 20 carbon atoms represented by R 1 to R 7 include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group,
- examples of the alkoxy group represented by R 1 to R 7 include a linear or branched alkoxy group having 1 to 4 carbon atoms, and specific examples thereof include a methoxy group, an ethoxy group, a propoxy group, and a butoxy group.
- the number of carbon atoms of the alkoxy group represented by R 1 to R 7 is preferably from 1 to 3, from the viewpoints of prevention of the morphological change of the film.
- the aryl group represented by R 1 to R 7 may or may not have a substituent, and examples thereof include substituted or unsubstituted phenyl groups.
- the substituent contained in the aryl group include an alkyl group having 1 to 10 carbon atoms, an alkoxy group, and a halogen atom.
- Specific examples of the aryl group include a phenyl group, a methylphenyl group (tolyl group), a dimethylphenyl group, and an ethylphenyl group.
- examples of the aralkyl group represented by R 1 to R 7 include a group represented by —R 15 —Ar 16 , provided that R 15 represents an alkylene group and Ar 16 represents a substituted or unsubstituted aryl group.
- Examples of the alkylene group represented by R 15 include a linear or branched alkylene group having 1 to 12 carbon atoms, and specific examples thereof include a methylene group, an ethylene group, an n-propylene group, an isopropylene group, an n-butylene group, an isobutylene group, a sec-butylene group, a tert-butylene group, an n-pentylene group, an isopentylene group, a neopentylene group, and a tert-pentylene group.
- the number of carbon atoms of the alkylene group represented by R 15 is preferably from 1 to 10, and more preferably from 1 to 6, from the viewpoints of compatibility and solubility.
- Examples of the substituted or unsubstituted aryl group represented by Ar 16 include the same groups as set forth above with respect to the aryl group represented by R 1 to R 7 in the formula (1), and examples of the substituent that the aryl group has also include the same groups as set forth above.
- aralkyl group represented by R 1 to R 7 examples include a benzyl group, a methylbenzyl group, a dimethylbenzyl group, a phenylethyl group, a methylphenylethyl group, a phenylpropyl group, and a phenylbutyl group.
- R 1 to R 7 in the formula (1) are each independently preferably a hydrogen atom, a halogen atom, a linear alkyl group having 1 to 10 carbon atoms, or a linear alkoxy group having 1 to 10 carbon atoms, and more preferably a hydrogen atom, from the viewpoints of a high electron transport capability and prevention of the morphological change of the film.
- examples of a combination of R 1 to R 7 in the formula (1) include a combination in which R 1 to R 7 are all hydrogen atoms, a combination in which six groups out of R 1 to R 7 are hydrogen atoms and the one group is a group other than a hydrogen atom, and a combination in which five groups out of R 1 to R 7 are hydrogen atoms and the two groups are groups other than a hydrogen atom.
- examples of the halogen atom represented by R 8 to R 10 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and from the viewpoints of the chemical stability, a fluorine atom and a chlorine atom are preferable.
- examples of the linear alkyl group with respect to the linear or branched alkyl group having 1 to 20 carbon atoms represented by R 8 to R 10 include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, and an n-decyl group.
- examples of the branched alkyl group with respect to the linear or branched alkyl group having 1 to 20 carbon atoms represented by R 8 to R 10 include an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an isodecyl group, a sec-decyl group
- the number of carbon atoms of the linear alkyl group represented by R 8 to R 10 is preferably from 1 to 10, and more preferably from 1 to 6, from the viewpoints of improvement of compatibility with a resin and prevention of film morphology. Further, in the formula (1), the number of carbon atoms of the branched alkyl group represented by R 8 to R 10 is preferably from 3 to 10, and more preferably from 3 to 6, from the viewpoints of improvement of the compatibility with a resin.
- examples of the aralkyl group represented by R 8 to R 10 include a group represented by —R 17 —Ar 18 , provided that R 17 represents an alkylene group and Ar 18 represents a substituted or unsubstituted aryl group.
- Examples of the alkylene group represented by R 17 include the same groups as set forth above with respect to R 15 of the group represented by —R 15 —Ar 16 .
- the number of carbon atoms of the alkylene group represented by R 17 is preferably from 1 to 10, and preferably from 1 to 6, from the viewpoints of prevention of the morphological change of the film.
- Examples of the aryl group represented by Ar 18 include the same groups as set forth above with respect to Ar 16 of the group represented by —R 15 —Ar 16 .
- specific examples of the aralkyl group represented by R 8 to R 10 include the specific examples of the aralkyl group represented by R 1 to R 7 .
- specific examples of the aryl group represented by R 8 to R 10 include the specific examples of the aryl group represented by R 1 to R 7 .
- R 11 represents a linear or branched alkylene group having 1 to 10 carbon atoms
- R 12 represents a linear or branched alkyl group having 1 to 10 carbon atoms.
- Examples of the linear or branched alkylene group having 1 to 10 carbon atoms represented by R 11 include the same groups as set forth above with respect to the specific examples of the alkylene group represented by R 15 in the group represented by —R 15 —Ar 16 .
- the number of carbon atoms of the alkylene group represented by R 11 is preferably from 1 to 10. Further, the alkylene group represented by R 11 is preferably a branched alkylene group having 1 to 10 carbon atoms.
- Examples of the linear or branched alkyl group having 1 to 10 carbon atoms represented by R 12 include the same groups as set forth above with respect to the specific examples of the alkyl group represented by R 8 to R 10 .
- the number of carbon atoms of the alkyl group represented by R 12 is preferably from 1 to 10.
- R 11 —O—R 12 which is represented by R 8 to R 10 , above all, a methoxymethyl group, an ethoxymethyl group, or a phenoxymethyl group is preferable.
- R 13 represents a single bond or a linear or branched alkylene group having 1 to 10 carbon atoms
- R 14 represents a linear or branched alkyl group having 1 to 10 carbon atoms, an aryl group, or an aralkyl group.
- Examples of the linear or branched alkylene group having 1 to 10 carbon atoms represented by R 13 include the same groups as set forth above with respect to the specific examples of the alkylene group represented by R 15 of the group represented by —R 15 —Ar 16 .
- the number of carbon atoms of the alkylene group represented by R 13 is preferably from 1 to 10. Further, the alkylene group represented by R 13 is preferably a branched alkylene group having 1 to 6 carbon atoms.
- Examples of the linear or branched alkyl group having 1 to 10 carbon atoms represented by R 14 include the same groups as set forth above with respect to the specific examples of the alkyl group represented by R 8 to R 10 .
- the number of carbon atoms of the alkyl group represented by R 14 is preferably from 1 to 10. Further, the alkyl group represented by R 14 is preferably a branched alkyl group having 1 to 10 carbon atoms.
- Examples of the aryl group represented by R 14 include the same groups as set forth above with respect to the specific examples of the aryl group represented by Ar 16 of the group represented by —R 15 —Ar 16 .
- the substituents introduced to the aryl group, the preferable groups, and the like are the same as for the aryl group represented by Ar 16 of the group represented by —R 5 —Ar 6 .
- Examples of the aralkyl group represented by R 14 include the same groups as set forth above with respect to the specific examples of the aralkyl group represented by R 8 to R 10 .
- the preferable groups are the same as for the aralkyl group represented by R 8 to R 10 .
- the binding position of R 10 in the formula (1) may be any of the 3-position, the 5-position, and the 6-position as long as it is a position other than the 2-position to which R 8 is bonded and the 4-position to which R 9 is bonded, and the 6-position is more preferable.
- R 8 to R 10 in the formula (1) are each independently preferably a hydrogen atom, a chlorine atom, a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, the aralkyl group represented by —R 17 —Ar 18 (R 17 represents a branched alkylene group having 3 to 10 carbon atoms and Ar 18 represents a substituted or unsubstituted phenyl group), —R 11 —O—R 12 (R 11 represents an alkylene group having 1 to 10 carbon atoms, and R 12 represents an alkyl group having 1 to 10 carbon atoms), —R 13 —CO—O—R 14 (R 13 represents a single bond or an alkylene group having 1 to 10 carbon atoms, and R 14 represents a linear or branched alkyl group having 1 to 10 carbon atoms or an aralkyl group); and more preferably a hydrogen atom, a linear alkyl group having 1 to 10
- R 8 to R 10 in the formula (1) may be any groups such that two or more groups of these groups are groups other than a hydrogen atom, but it is preferable that one or more groups of R 8 to R 10 is each an organic group having 1 or more carbon atoms (that is, an alkyl group, an aralkyl group, an aryl group, —R 1 —O—R 12 , or —R 13 —CO—O—R 4 ), and it is more preferable that two or more groups of R 8 to R 10 is each an organic group having 1 or more carbon atoms.
- R 8 and R 9 in the formula (1) are groups other than a hydrogen atom (R 10 is a hydrogen atom or a group other than a hydrogen atom), and it is more preferable that R 10 is a hydrogen atom, and R 8 and R 9 are a group other than a hydrogen atom.
- the electron transport material represented by the formula (1) is preferably the electron transport material, in which R 1 to R 7 each independently represent a hydrogen atom, a halogen atom, or an alkyl group, R 8 and R 9 represent a linear or branched alkyl group having 1 to 10 carbon atoms, or an aralkyl group, and R 10 is a hydrogen atom; in particular, in which R 1 to R 7 each independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 10 carbon atoms, further, R 8 and R 9 are both a branched alkyl group having 3 to 10 carbon atoms or an aralkyl group represented by —R 7 —Ar 8 (R 17 is a branched alkylene group having 3 to 10 carbon atoms and Ar 18 is an unsubstituted phenyl group), and R 10 represents a hydrogen atom, from the viewpoints of improvement of compatibility with a resin and prevention of film morphology.
- the electron transport material represented by the formula (1) is synthesized by a known method.
- Route 2 By reacting the obtained acid chloride with a phenol derivative (for example, 2,4-xylenol) in the presence of a base catalyst (for example, pyridine, piperidine, and triethylamine) to obtain the compound of the formula (1) in which X is an oxygen atom.
- a phenol derivative for example, 2,4-xylenol
- a base catalyst for example, pyridine, piperidine, and triethylamine
- the electron transport material according to the present exemplary embodiment has a high electron transport capability and a high compatibility with a resin, and hardly causes aggregation or diffusion of the molecules in a system, and therefore, it hardly causes a morphological change in a layer.
- the electron transport material according to the present exemplary embodiment is suitable for, for example, a photosensitive layer of an electrophotographic photoreceptor (in particular, a single layer type photoreceptor) as described later.
- the electrophotographic photoreceptor according to the present exemplary embodiment has a conductive substrate and a photosensitive layer provided on the conductive substrate, in which the photosensitive layer includes an electron transport material represented by the formula (1) (hereinafter referred to as a “specific electron transport material” in some cases).
- the photosensitive layer includes an electron transport material represented by the formula (1) (hereinafter referred to as a “specific electron transport material” in some cases).
- the photosensitive layer may be a function integration type photosensitive layer (single layer type photosensitive layer) having both a charge transport capability and a charge generating capability, and may be a function separation type photosensitive layer including a charge transport layer and a charge generating layer. Further, in the function separation type photosensitive layer, the specific electron transport material is included in the charge transport layer.
- a positively charged organic photoreceptor (hereinafter simply referred to as a “photoreceptor” or a “single layer type photoreceptor” in some cases) having a single layer type photosensitive layer on a conductive substrate will be described in detail with reference to the drawings.
- FIG. 1 schematically shows a cross-sectional view of a part of the electrophotographic photoreceptor 10 according to the present exemplary embodiment.
- the electrophotographic photoreceptor 10 shown in FIG. 1 includes a conductive substrate 3 , and has a structure in which an undercoat layer 1 and a single layer type photosensitive layer 2 are provided in this order on the conductive substrate 3 .
- the undercoat layer 1 is a layer which is provided, as desired. That is, the single layer type photosensitive layer 2 may be provided directly or through the undercoat layer 1 on the conductive substrate 3 .
- a protective layer may be provided on a single layer type photosensitive layer 2 , as desired.
- the conductive substrate examples include metal plates, metal drums, and metal belts containing a metal (such as aluminum, copper, zinc, chromium, nickel, molybdenum, vanadium, indium, gold, and platinum), and alloys thereof (such as stainless steel). Further, other examples of the conductive substrate include papers, resin films, and belts which are coated, deposited, or laminated with a conductive compound (such as a conductive polymer and indium oxide), a metal (such as aluminum, palladium, and gold), or alloys thereof.
- a conductive compound such as a conductive polymer and indium oxide
- a metal such as aluminum, palladium, and gold
- the surface of the conductive substrate is preferably roughened so as to have a centerline average roughness (Ra) of 0.04 ⁇ m to 0.5 ⁇ m sequentially to prevent interference fringes which are formed when irradiated with laser light.
- Ra centerline average roughness
- surface roughening for preventing interference fringes is not particularly necessary, but occurrence of defects due to the irregularities on the surface of the conductive substrate is prevented, which is thus suitable for achieving a longer service life.
- Examples of the method for surface roughening include wet honing in which an abrasive suspended in water is blown onto a support, centerless grinding in which a support is continuously ground by pressing a conductive substrate onto a rotating grind stone, and anodic oxidation treatment.
- the method for surface roughening include a method for surface roughening by forming a layer of a resin in which conductive or semiconductive particles are dispersed in the resin so that the surface roughening is achieved by forming a layer on the surface of a conductive substrate, while not roughening the surface of the conductive substrate.
- an oxide film is formed on the surface of a conductive substrate by anodic oxidation in which a metal (for example, aluminum) conductive substrate as an anode is anodized in an electrolyte solution.
- the electrolyte solution include a sulfuric acid solution and an oxalic acid solution.
- the porous anodic oxide film formed by anodic oxidation as it is chemically active, easily contaminated and has a large resistance variation depending on the environment.
- a sealing treatment in which for a porous anodic oxide film, fine pores of the oxide film are sealed by cubical expansion caused by a hydration in pressurized water vapor or boiled water (to which a metallic salt such as a nickel salt may be added) to transform the anodic oxide into a more stable hydrated oxide.
- the film thickness of the anodic oxide film is preferably from 0.3 ⁇ m to 15 ⁇ m.
- a barrier property against injection tends to be exerted and an increase in the residual potential due to the repeated use tends to be prevented.
- the conductive substrate may be subjected to a treatment with an acidic aqueous solution or a boehmite treatment.
- the treatment with an acidic treatment solution is carried out as follows. First, an acidic treatment solution including phosphoric acid, chromic acid, and hydrofluoric acid is prepared.
- the mixing ratio of phosphoric acid, chromic acid, and hydrofluoric acid in the acidic treatment solution is, for example, a ratio such that from 10% by weight to 11% by weight of phosphoric acid, from 3% by weight to 5% by weight of chromic acid, and from 0.5% by weight to 2% by weight of hydrofluoric acid.
- the concentration of the total acid components is preferably in the range of 13.5% by weight to 18% by weight.
- the treatment temperature is, for example, preferably from 42° C. to 48° C.
- the film thickness of the film is preferably from 0.3 ⁇ m to 15 ⁇ m.
- the boehmite treatment is carried out by immersing the substrate in pure water at a temperature of 90° C. to 100° C. for 5 minutes to 60 minutes, or by bringing it into contact with heated water vapor at a temperature of 90° C. to 120° C. for 5 minutes to 60 minutes.
- the film thickness of the film is preferably from 0.1 ⁇ m to 5 ⁇ m.
- the film may further be subjected to an anodic oxidation treatment using an electrolyte solution which sparingly dissolves the film, such as adipic acid, boric acid, borate, phosphate, phthalate, maleate, benzoate, tartrate, and citrate solutions.
- the undercoat layer is, for example, a layer including inorganic particles and a binder resin.
- inorganic particles examples include inorganic particles having powder resistance (volume resistivity) of about 10 2 ⁇ cm to 10 11 ⁇ cm.
- metal oxide particles such as tin oxide particles, titanium oxide particles, zinc oxide particles, and zirconium oxide particles are preferable, and zinc oxide particles are more preferable.
- the specific surface area of the inorganic particles as measured by a BET method is, for example, preferably 10 m 2 /g or more.
- the volume average particle diameter of the inorganic particles is, for example, preferably from 50 nm to 2000 nm (preferably from 60 nm to 1000 nm).
- the content of the inorganic particles is, for example, preferably from 10% by weight to 80% by weight, and more preferably from 40% by weight to 80% by weight, based on the binder resin.
- the inorganic particles may be the ones which have been subjected to a surface treatment.
- the inorganic particles which have been subjected to different surface treatments or have different particle diameters may be used in combination of two or more kinds.
- the surface treatment agent examples include a silane coupling agent, a titanate coupling agent, an aluminum coupling agent, and a surfactant.
- the silane coupling agent is preferable, and a silane coupling agent having an amino group is more preferable.
- silane coupling agent having an amino group examples include 3-aminopropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, and N,N-bis(2-hydroxyethyl)-3-aminopropyltriethoxysilane, but are not limited thereto.
- silane coupling agents may be used as a mixture of two or more kinds thereof.
- a silane coupling agent having an amino group and the other silane coupling agent may be used in combination.
- the other silane coupling agent include vinyltrimethoxysilane, 3-methacryloxypropyl-tris(2-methoxyethoxy)silane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, vinyltriacetoxysilane, 3-mercaptopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N,N-bis(2-hydroxyethyl)-3-aminopropyltriethoxy
- the surface treatment method using a surface treatment agent may be any one of known methods, and may be either a dry method or a wet method.
- the amount of the surface treatment agent for treatment is, for example, preferably from 0.5% by weight to 10% by weight, based on the inorganic particles.
- inorganic particles and an electron acceptive compound (acceptor compound) are preferably included in the undercoat layer from the viewpoint of superior long-term stability of electrical characteristics and carrier blocking property.
- Examples of the electron acceptive compound include electron transport materials such as quinone compounds such as chloranil and bromanil; tetracyanoquinodimethane compounds; fluorenone compounds such as 2,4,7-trinitrofluorenone and 2,4,5,7-tetranitro-9-fluorenone; oxadiazole compounds such as 2-(4-biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole, 2,5-bis(4-naphthyl)-1,3,4-oxadiazole, and 2,5-bis(4-diethylaminophenyl)-1,3,4-oxadiazole; xanthone compounds; thiophene compounds; and diphenoquinone compounds such as 3,3′,5,5′-tetra-t-butyldiphenoquinone.
- quinone compounds such as chloranil and bromanil
- tetracyanoquinodimethane compounds fluorenone
- the electron acceptive compound compounds having an anthraquinone structure are preferable.
- the electron acceptive compounds having an anthraquinone structure hydroxyanthraquinone compounds, aminoanthraquinone compounds, aminohydroxyanthraquinone compounds, and the like are preferable, and specifically, anthraquinone, alizarin, quinizarin, anthrarufin, purpurin, and the like are preferable.
- the electron acceptive compound may be included as dispersed with the inorganic particles in the undercoat layer, or may be included as attached to the surface of the inorganic particles.
- Examples of the method of attaching the electron acceptive compound to the surface of the inorganic particles include a dry method and a wet method.
- the dry method is a method for attaching an electron acceptive compound to the surface of the inorganic particles, in which the electron acceptive compound is added dropwise to the inorganic particles or sprayed thereto together with dry air or nitrogen gas, either directly or in the form of a solution in which the electron acceptive compound is dissolved in an organic solvent, while the inorganic particles are stirred with a mixer or the like having a high shearing force.
- the addition or spraying of the electron acceptive compound is preferably carried out at a temperature not higher than the boiling point of the solvent.
- the inorganic particles may further be subjected to baking at a temperature of 100° C. or higher. The baking may be carried out at any temperature and time without limitation, by which desired electrophotographic characteristics may be obtained.
- the wet method is a method for attaching an electron acceptive compound to the surface of the inorganic particles, in which the inorganic particles are dispersed in a solvent by means of stirring, ultrasonic wave, a sand mill, an attritor, a ball mill, or the like, then the electron acceptive compound is added and the mixture is further stirred or dispersed, and thereafter, the solvent is removed.
- the solvent is removed by filtration or distillation.
- the particles may further be subjected to baking at a temperature of 100° C. or higher. The baking may be carried out at any temperature and time without limitation, in which desired electrophotographic characteristics may be obtained.
- the moisture contained in the inorganic particles may be removed prior to the addition of an electron acceptive compound, and examples of a method for removing the moisture include a method for removing the moisture by stirring and heating the inorganic particles in a solvent or by azeotropic removal with the solvent.
- the attachment of the electron acceptive compound may be carried out before or after the inorganic particles are subjected to a surface treatment using a surface treatment agent, and the attachment of the electron acceptive compound may be carried out at the same time with the surface treatment using a surface treatment agent.
- the content of the electron acceptive compound is, for example, preferably from 0.01% by weight to 20% by weight, and more preferably from 0.01% by weight to 10% by weight, based on the inorganic particles.
- binder resin used in the undercoat layer examples include known materials, such as well-known polymeric compounds such as acetal resins (for example, polyvinylbutyral), polyvinyl alcohol resins, polyvinyl acetal resins, casein resins, polyamide resins, cellulose resins, gelatins, polyurethane resins, polyester resins, unsaturated polyether resins, methacrylic resins, acrylic resins, polyvinyl chloride resins, polyvinyl acetate resins, vinyl chloride-vinyl acetate-maleic anhydride resins, silicone resins, silicone-alkyd resins, urea resins, phenol resins, phenol-formaldehyde resins, melamine resins, urethane resins, alkyd resins, and epoxy resins; zirconium chelate compounds; titanium chelate compounds; aluminum chelate compounds; titaniumalkoxide compounds; organic titanium compounds; and silane coupling agents.
- acetal resins for example,
- binder resins used in the undercoat layer include charge transport resins having charge transport groups, and conductive resins (for example, polyaniline).
- thermosetting resins such as urea resins, phenol resins, phenol-formaldehyde resins, melamine resins, urethane resins, unsaturated polyester resins, alkyd resins, and epoxy resins
- resins obtained by a reaction of a curing agent and at least one kind of resin selected from the group consisting of polyamide resins, polyester resins, polyether resins, methacrylic resins, acrylic resins, polyvinyl alcohol resins, and polyvinyl acetal resins are suitable.
- the mixing ratio is set as appropriate.
- Various additives may be used for the undercoat layer to improve electrical characteristics, environmental stability, or image quality.
- additives examples include known materials such as the polycyclic condensed type or azo type of the electron transport pigments, zirconium chelate compounds, titanium chelate compounds, aluminum chelate compounds, titanium alkoxide compounds, organic titanium compounds, and silane coupling agents.
- a silane coupling agent which is used for surface treatment of inorganic particles as described above, may also be added to the undercoat layer as an additive.
- silane coupling agent as an additive examples include vinyltrimethoxysilane, 3-methacryloxypropyl-tris(2-methoxyethoxy)silane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, vinyltriacetoxysilane, 3-mercaptopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethylmethoxysilane, N,N-bis(2-hydroxyethyl)-3-aminopropyltriethoxysilane, and 3-chloropropyltrimethoxysilane.
- zirconium chelate compounds examples include zirconium butoxide, zirconium ethylacetoacetate, zirconium triethanolamine, acetylacetonate zirconium butoxide, ethylacetoacetate zirconium butoxide, zirconium acetate, zirconium oxalate, zirconium lactate, zirconium phosphonate, zirconium octanoate, zirconium naphthenate, zirconium laurate, zirconium stearate, zirconium isostearate, methacrylate zirconium butoxide, stearate zirconium butoxide, and isostearate zirconium butoxide.
- titanium chelate compounds examples include tetraisopropyl titanate, tetranormalbutyl titanate, butyl titanate dimer, tetra(2-ethylhexyl) titanate, titanium acetyl acetonate, polytitaniumacetyl acetonate, titanium octylene glycolate, titanium lactate ammonium salt, titanium lactate, titanium lactate ethyl ester, titanium triethanol aminate, and polyhydroxy titanium stearate.
- aluminum chelate compounds examples include aluminum isopropylate, monobutoxy aluminum diisopropylate, aluminum butylate, diethylacetoacetate aluminum diisopropylate, and aluminum tris(ethylacetoacetate).
- additives may be used alone, or as a mixture or a polycondensate of plural compounds.
- the Vickers hardness of the undercoat layer is preferably 35 or more.
- the surface roughness (ten point height of irregularities) of the undercoat layer is adjusted in the range of from (1/4) n ⁇ to (1/2) ⁇ , in which X represents the wavelength of the laser for exposure and n represents a refractive index of the upper layer, in order to prevent a moire image.
- Resin particles and the like may be added in the undercoat layer in order to adjust the surface roughness.
- the resin particles include silicone resin particles and crosslinked polymethyl methacrylate resin particles.
- the surface of the undercoat layer may be polished in order to adjust the surface roughness. Examples of the polishing method include buffing grinding, a sandblasting treatment, wet honing, and a grinding treatment.
- the formation of the undercoat layer is not particularly limited, and well-known forming methods are used. However, the formation of the undercoat layer is carried out by, for example, forming a coating film by a coating liquid for forming an undercoat layer, which is obtained by adding the components above to a solvent, and drying the coating film, followed by heating, as desired.
- Examples of the solvent for forming the coating liquid for forming an undercoat layer include known organic solvents, such as alcohol solvents, aromatic hydrocarbon solvents, hydrocarbon halide solvents, ketone solvents, ketone alcohol solvents, ether solvents, and ester solvents.
- organic solvents such as alcohol solvents, aromatic hydrocarbon solvents, hydrocarbon halide solvents, ketone solvents, ketone alcohol solvents, ether solvents, and ester solvents.
- solvents include ordinary organic solvents such as methanol, ethanol, n-propanol, iso-propanol, n-butanol, benzyl alcohol, methyl cellosolve, ethyl cellosolve, acetone, methyl ethyl ketone, cyclohexanone, methyl acetate, ethyl acetate, n-butyl acetate, dioxane, tetrahydrofuran, methylene chloride, chloroform, chlorobenzene, and toluene.
- organic solvents such as methanol, ethanol, n-propanol, iso-propanol, n-butanol, benzyl alcohol, methyl cellosolve, ethyl cellosolve, acetone, methyl ethyl ketone, cyclohexanone, methyl acetate, ethyl acetate, n-butyl
- Examples of a method for dispersing inorganic particles in preparing the coating liquid for forming an undercoat layer include known methods such as methods using a roll mill, a ball mill, a vibration ball mill, an attritor, a sand mill, a colloid mill, a paint shaker, and the like.
- Examples of a method for coating the coating liquid for forming an undercoat layer onto a conductive substrate include ordinary methods such as a blade coating method, a wire bar coating method, a spray coating method, a dip coating method, a bead coating method, an air knife coating method, and a curtain coating method.
- the film thickness of the undercoat layer is set to a range of, for example, preferably 15 ⁇ m or more, and more preferably from 20 ⁇ m to 50 ⁇ m.
- an intermediate layer may be provided between the undercoat layer and the photosensitive layer.
- the intermediate layer is, for example, a layer including a resin.
- the resin used in the intermediate layer include polymeric compounds such as acetal resins (for example, polyvinylbutyral), polyvinyl alcohol resins, polyvinyl acetal resins, casein resins, polyamide resins, cellulose resins, gelatins, polyurethane resins, polyester resins, methacrylic resins, acrylic resins, polyvinyl chloride resins, polyvinyl acetate resins, vinyl chloride-vinyl acetate-maleic anhydride resins, silicone resins, silicone-alkyd resins, phenol-formaldehyde resins, and melamine resins.
- acetal resins for example, polyvinylbutyral
- polyvinyl alcohol resins for example, polyvinyl alcohol resins, polyvinyl acetal resins, casein resins, polyamide resins, cellulose resins, gelatins, polyurethane resins, polyester resins, me
- the intermediate layer may be a layer including an organic metal compound.
- organic metal compound used in the intermediate layer include organic metal compounds containing a metal atom such as zirconium, titanium, aluminum, manganese, and silicon.
- These compounds used in the intermediate layer may be used alone or as a mixture or a polycondensate of plural compounds.
- the intermediate layer is preferably a layer including an organometallic compound containing a zirconium atom or a silicon atom.
- the formation of the intermediate layer is not particularly limited, and well-known forming methods are used. However, the formation of the intermediate layer is carried out, for example, by forming a coating film by a coating liquid for forming an intermediate layer, which is obtained by adding the components above to a solvent, and drying the coating film, followed by heating, as desired.
- a coating method for forming an intermediate layer ordinary methods such as a dip coating method, an extrusion coating method, a wire bar coating method, a spray coating method, a blade coating method, a knife coating method, and a curtain coating method are used.
- the film thickness of the intermediate layer is set to, for example, preferably a range of 0.1 ⁇ m to 3 ⁇ m. Further, the intermediate layer may be used as an undercoat layer.
- the single layer type photosensitive layer may include a binder resin, a charge generating material, a hole transport material, and an electron transport material, and other additives, as desired.
- the binder resin is not particularly limited, but examples thereof include polycarbonate resins, polyester resins, polyarylate resins, methacrylic resins, acrylic resins, polyvinyl chloride resins, polyvinylidene chloride resins, polystyrene resins, polyvinyl acetate resins, styrene-butadiene copolymers, vinylidene chloride-acrylonitrile copolymers, vinyl chloride-vinyl acetate copolymers, vinyl chloride-vinyl acetate-maleic anhydride copolymers, silicone resins, silicone-alkyd resins, phenol-formaldehyde resins, styrene-alkyd resins, poly-N-vinyl carbazole, and polysilane. These binder resins may be used alone or as a mixture of two or more kinds thereof.
- binder resins from the viewpoint of prevention of segregation of electron transport materials, particularly, polycarbonate resins and polyarylate resins are preferable.
- binder resin for example, polycarbonate resins having a viscosity average molecular weight of 30000 to 80000 and polyarylate resins having a viscosity average molecular weight of 30000 to 80000 are preferable.
- the content of the binder resin based on the total solid content of the photosensitive layer is, for example, from 35% by weight to 60% by weight, and preferably from 40% by weight to 55% by weight.
- Examples of the charge generating material include azo pigments such as bisazo and trisazo pigments; condensed aromatic pigments such as dibromoanthanthrone pigments; perylene pigments; pyrrolopyrrole pigments; phthalocyanine pigments; zinc oxides; and trigonal selenium.
- azo pigments such as bisazo and trisazo pigments
- condensed aromatic pigments such as dibromoanthanthrone pigments
- perylene pigments such as pyrrolopyrrole pigments
- phthalocyanine pigments such as zinc oxides; and trigonal selenium.
- metal phthalocyanine pigments or metal-free phthalocyanine pigments as the charge generating material, and specifically, hydroxygallium phthalocyanine disclosed in JP-A-5-263007, JP-A-5-279591, and the like; chlorogallium phthalocyanine disclosed in JP-A-5-98181 and the like; dichlorotin phthalocyanine disclosed in JP-A-5-140472, JP-A-5-140473, and the like; and titanyl phthalocyanine disclosed in JP-A-4-189873 and the like are more preferable.
- condensed aromatic pigments such as dibromoanthanthrone; thioindigo pigments; porphyrazine compounds; zinc oxides; trigonal selenium; bisazo pigments disclosed in JP-A-2004-78147 and JP-A-2005-181992; and the like are preferable.
- an inorganic pigment is preferable to correspond to a case where a light source having an exposure wavelength of from 380 nm to 500 nm is used, and, a metal phthalocyanine pigment or a metal-free phthalocyanine pigment is preferable to correspond to a case where a light source having an exposure wavelength of from 700 nm to 800 nm is used.
- At least one selected from a hydroxygallium phthalocyanine pigment and a chlorogallium phthalocyanine pigment is preferably used.
- these pigments may be used alone or in combination thereto, as desired. Further, as the charge generating material, a hydroxygallium phthalocyanine pigment is preferable from the viewpoints of a high sensitivity of a photoreceptor and prevention of dot defects of an image.
- the hydroxygallium phthalocyanine pigment is not particularly limited, but a V-type hydroxygallium phthalocyanine pigment is preferable.
- the hydroxygallium phthalocyanine pigment for example, a hydroxygallium phthalocyanine pigment having a maximum peak wavelength in the range of from 810 nm to 839 nm in a spectral absorption spectrum in a wavelength region of from 600 nm to 900 nm is preferable from the viewpoint that it imparts more excellent dispersibility.
- a hydroxygallium phthalocyanine pigment having a maximum peak wavelength in the range of from 810 nm to 839 nm in a spectral absorption spectrum in a wavelength region of from 600 nm to 900 nm is preferable from the viewpoint that it imparts more excellent dispersibility.
- the hydroxygallium phthalocyanine pigment is used as a material for an electrophotographic photoreceptor, excellent dispersibility, sufficient sensitivity, chargeability, and characteristics of dark attenuation are easily obtained.
- the hydroxygallium phthalocyanine pigment having a maximum peak wavelength in the range from 810 nm to 839 nm preferably has an average particle diameter in a specific range and a BET specific surface area in a specific range.
- the average particle diameter is preferably 0.20 ⁇ m or less, and more preferably from 0.01 ⁇ m to 0.15 ⁇ m.
- the BET specific surface area is preferably 45 m 2 /g or more, more preferably 50 m 2 /g or more, and particularly preferably from 55 m 2 /g to 120 m 2 /g.
- An average particle diameter is a volume average particle diameter (d50 average particle diameter) and a value measured by a laser diffraction scattering particle size distribution analyzer LA-700 (manufactured by Horiba Ltd.). Further, the BET specific surface area is a value measured by a nitrogen substitution method using a BET specific surface area analyzer (FLOWSORB 112300, manufactured by Shimadzu Corporation).
- the pigment particles are coarsened or aggregates of pigment particles are formed. Further, the characteristics such as dispersibility, sensitivity, chargeability, and dark attenuation characteristics tend to be deteriorated to result in image defect in some cases.
- a maximum particle diameter (a maximum value of a primary particle diameter) of the hydroxygallium phthalocyanine pigment is preferably 1.2 ⁇ m or less, more preferably 1.0 ⁇ m or less, and still more preferably 0.3 ⁇ m or less. When the maximum particle diameter exceeds the above range, black spots tend to be formed.
- the hydroxygallium phthalocyanine pigment preferably has an average particle diameter of 0.2 ⁇ m or less, the maximum particle diameter of 1.2 ⁇ m or less and the specific surface area of 45 m 2 /g or more.
- the hydroxygallium phthalocyanine pigment is preferably a V type one which has diffraction peaks at at least 7.3°, 16.0°, 24.9°, and 28.0° by a Bragg angle (2 ⁇ 0.2°) in an X-ray diffraction spectrum obtained using CuK ⁇ characteristic X-ray.
- the chlorogallium phthalocyanine pigment is not particularly limited, but preferably has diffraction peaks at 7.4°, 16.6°, 25.5°, and 28.3° by a Bragg angle (2 ⁇ 0.20) in an X-ray diffraction spectrum obtained using CuK ⁇ characteristic X-ray, whereby excellent sensitivity for an electrophotographic photoreceptor material is obtained.
- Suitable maximum peak wavelength of the spectral absorption spectrum, the average particle diameter, the maximum particle diameter, and the specific surface area value of the chlorogallium phthalocyanine pigment are the same as those of the hydroxygallium phthalocyanine pigment.
- the content of the charge generating material based on the total solid content of the photosensitive layer is preferably from 1% by weight to 5% by weight, and more preferably from 1.2% by weight to 4.5% by weight.
- Examples of the hole transport material include triarylamine compounds, benzidine compounds, arylalkane compounds, aryl-substituted ethylene compounds, stilbene compounds, anthracene compounds, and hydrazone compounds. These charge transport materials may be used alone or in combination of two or more kinds thereof, but are not limited thereto.
- the hole transport material is preferably a compound represented by the following formula (B-1), a compound represented by the following formula (B-2), and a compound represented by the following formula (B-3) from the viewpoint of charge mobility.
- R B1 represents a hydrogen atom or a methyl group.
- n11 represents 1 or 2.
- Ar B1 and Ar B2 each independently represent a substituted or unsubstituted aryl group, —C 6 H 4 —C(R B3 ) ⁇ C(R B4 )(R B5 ), or —C 6 H 4 —CH ⁇ CH—CH ⁇ C(R B6 )(R B7 ), and R B3 to R B7 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
- the substituent represents a halogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or a substituted amino group substituted with an alkyl group having 1 to 3 carbon atoms.
- R B8 and R B8′ may be the same as or different from each other and each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkoxy group having 1 to 5 carbon atoms.
- R B9 , R B9′ , R B10′ , and R Bl0′ may be the same as or different from each other and each independently represent a halogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a substituted amino group substituted with an alkyl group having 1 or 2 carbon atoms, a substituted or unsubstituted aryl group, —C(R B11 ) ⁇ C(R B12 ) (R B13 ), or —CH ⁇ CH—CH ⁇ C(R B14 ) (R B15 ), and R B1 to R B15 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
- m12, m13, n12, and n13 each independently represent an integer of 0 to 2.
- R B16 and R B16′ may be the same as or different from each other and each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkoxy group having 1 to 5 carbon atoms.
- R B17 , R B17′ , R B18 , and R B18′ may be the same as or different from each other and each independently represent a halogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a substituted amino group substituted with an alkyl group having 1 or 2 carbon atoms, a substituted or unsubstituted aryl group, —C(R B19 ) ⁇ C(R B20 ) (R B21 ), or —CH ⁇ CH—CH ⁇ C(R B22 ) (R B23 ), and R B19 to R B23 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
- m14, m15, n14, and n15 each independently represent an integer of 0 to 2.
- the compound represented by the formula (B-1), the compound represented by the formula (B-2), and the compound represented by the formula (B-3), the compound represented by the formula (B-1) having “—C 6 H 4 —CH ⁇ CH—CH ⁇ C(R B6 ) (R B7 )” and the compound represented by the formula (B-2) having “—CH ⁇ CH—CH ⁇ C(R B14 ) (R B15 )” are preferable.
- the content of the hole transport material based on the total solid content of the photosensitive layer is preferably from 10% by weight to 40% by weight, and more preferably from 20% by weight to 35% by weight. Further, the content of the hole transport material is the content of the entire hole transport materials in the case of using a combination of plural kinds of hole transport materials.
- At least an electron transport material represented by the formula (1) is used, but may be used alone, or may be used in combination of other electron transport materials, as desired, within a range not adversely affecting the invention.
- the content of the electron transport material represented by the formula (1) based on the total solid content of the photosensitive layer is preferably from 1% by weight to 30% by weight, and more preferably from 5% by weight to 20% by weight.
- the electron transport material it is preferable to use other electron transport materials in the amount of 50% by weight or less based on the total amount of the electron transport material.
- Examples of the other electron transport materials include electron transport compounds, such as fluorenone derivatives other than the electron transport material represented by the formula (1); quinone compounds such as p-benzoquinone, chloranil, bromanil, and anthraquinone; tetracyanoquinodimethane compounds; fluorenone compounds such as 2,4,7-trinitrofluorenone; xanthone compounds; benzophenone compounds; cyanovinyl compounds; and ethylene compounds.
- electron transport compounds such as fluorenone derivatives other than the electron transport material represented by the formula (1)
- quinone compounds such as p-benzoquinone, chloranil, bromanil, and anthraquinone
- tetracyanoquinodimethane compounds fluorenone compounds such as 2,4,7-trinitrofluorenone
- xanthone compounds such as 2,4,7-trinitrofluorenone
- benzophenone compounds such as 2,4,7-trinitrofluorenone
- the ratio of the hole transport material to the electron transport material is preferably from 50/50 to 90/10, and more preferably from 60/40 to 80/20, in terms of a weight ratio (hole transport material/electron transport material).
- the “electron transport materials” in this ratio is a sum of the combination of the materials.
- the single layer type photosensitive layer may include other known additives such as a surfactant, an antioxidant, a light stabilizer, and a heat stabilizer. Further, in the case where the single layer type photosensitive layer is a surface layer, it may include fluorine resin particles, silicone oils, or the like.
- the single layer type photosensitive layer is formed by using a coating liquid for forming a photosensitive layer, which is prepared by adding the above components in a solvent.
- the solvent examples include ordinary organic solvents, such as aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; ketones such as acetone and 2-butanone; aliphatic hydrocarbon halides such as methylene chloride, chloroform, and ethylene chloride; and cyclic or linear ethers such as tetrahydrofuran and ethyl ether. These solvents may be used alone or in combination of two or more kinds thereof.
- aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene
- ketones such as acetone and 2-butanone
- aliphatic hydrocarbon halides such as methylene chloride, chloroform, and ethylene chloride
- cyclic or linear ethers such as tetrahydrofuran and ethyl ether.
- a media dispersing machine such as a ball mill, a vibrating ball mill, an attritor, a sand mill, and a horizontal sand mill, or a medialess dispersing machine such as a stirrer, an ultrasonic dispersing machine, a roll mill, and a high-pressure homogenizer is used.
- Examples of the high-pressure homogenizer include a collision system in which the particles are dispersed by causing the dispersion to collide against liquid or against walls under a high pressure, and a penetration system in which the particles are dispersed by causing the dispersion to penetrate through a fine flow path under a high pressure.
- Examples of a method for coating the coating liquid for forming a photosensitive layer onto the undercoat layer include a dip coating method, an extrusion coating method, a wire bar coating method, a spray coating method, a blade coating method, a knife coating method, and a curtain coating method.
- the film thickness of the single layer type photosensitive layer is set to a range of preferably from 5 ⁇ m to 60 m, more preferably from 5 ⁇ m to 50 ⁇ m, and still more preferably from 10 ⁇ m to 40 ⁇ m.
- the image forming apparatus is provided with an electrophotographic photoreceptor, a charging unit that charges the surface of the electrophotographic photoreceptor, an electrostatic latent image forming unit that forms an electrostatic latent image on the surface of a charged electrophotographic photoreceptor, a developing unit that develops the electrostatic latent image formed on the surface of the electrophotographic photoreceptor by a developer including a toner to form a toner image, and a transfer unit that transfers the toner image onto a surface of a recording medium.
- the electrophotographic photoreceptor according to the present exemplary embodiment is applied as the electrophotographic photoreceptor.
- known image forming apparatuses provided with a device including a fixing unit that fixes a toner image transferred to the surface of a recording medium; a direct transfer type device that directly transfers the toner image formed on the surface of the electrophotographic photoreceptor to a recording medium; an intermediate transfer type device that primarily transfers the toner image formed on the surface of the electrophotographic photoreceptor on the surface of the intermediate transfer member, and secondarily transfers the toner image transferred to the surface of an intermediate transfer member to the surface of the recording medium; a device provided with a cleaning unit that cleans the surface of the electrophotographic photoreceptor before charging, after the transfer of the toner image; a device provided with a charge erasing unit that erases charges by irradiating erasing light onto the surface of an image holing member before charging, after the transfer of the toner image; a device provided with an electrophotographic photoreceptor heating unit that increases the temperature of the electrophotographic photoreceptor to
- the transfer unit for example, a configuration in which an intermediate transfer member to the surface of which the toner image is transferred, a primary transfer unit that primarily transfers a toner image formed on the surface of an image holding member to the surface of the intermediate transfer member, and a secondary transfer unit that secondarily transfers the toner image transferred to the surface of the intermediate transfer member on the surface of the recording medium is applied.
- the image forming apparatus is any one of a dry development type image forming apparatus and a wet development type (development type using a liquid developer) image forming apparatus.
- a part provided with the electrophotographic photoreceptor may be a cartridge structure (process cartridge) that is detachable from an image forming apparatus.
- a process cartridge including the electrophotographic photoreceptor according to the present exemplary embodiment is suitably used.
- the process cartridge may include, in addition to the electrophotographic photoreceptor, for example, at least one selected from the group consisting of a charging means, an electrostatic latent image forming unit, a developing unit, and a transfer unit.
- FIG. 2 is a schematic structural view showing an example of the image forming apparatus according to the present exemplary embodiment.
- the image forming apparatus 100 is provided with a process cartridge 300 provided with an electrophotographic photoreceptor 7 as shown in FIG. 2 , an exposure device 9 (one example of the electrostatic latent image forming unit), a transfer device 40 (primary transfer device), and an intermediate transfer member 50 . Further, in the image forming apparatus 100 , the exposure device 9 is arranged at a position where the exposure device 9 may radiate light onto the electrophotographic photoreceptor 7 through an opening in the process cartridge 300 , and the transfer device 40 is arranged at a position opposite to the electrophotographic photoreceptor 7 by the intermediary of the intermediate transfer member 50 . The intermediate transfer member 50 is arranged to contact partially the electrophotographic photoreceptor 7 .
- the apparatus also includes a secondary transfer device that transfers a toner image transferred onto the intermediate transfer member 50 to a recording medium (for example, paper).
- a secondary transfer device that transfers a toner image transferred onto the intermediate transfer member 50 to a recording medium (for example, paper).
- the intermediate transfer member 50 , the transfer device 40 (primary transfer device), and the secondary transfer device correspond to an example of the transfer unit.
- the process cartridge 300 in FIG. 2 supports, in a housing, the electrophotographic photoreceptor 7 , a charging device 8 (one example of the charging unit), a developing device 11 (one example of the developing unit), and a cleaning device 13 (one example of the cleaning unit) integrally.
- the cleaning device 13 has a cleaning blade (one example of the cleaning member) 131 , and the cleaning blade 131 is arranged so as to be in contact with the surface of the electrophotographic photoreceptor 7 .
- the cleaning member is not an embodiment of the cleaning blade 131 , may be a conductive or insulating fibrous member, and may be used alone or in combination with the cleaning blade 131 .
- FIG. 2 shows an example that includes fibrous member 132 (roll shape) that supplies a lubricant 14 to the surface of the electrophotographic photoreceptor 7 as the image forming apparatus, and a fibrous member 133 (flat brush shape) that assists in cleaning, but these members are disposed, as desired.
- fibrous member 132 roll shape
- fibrous member 133 flat brush shape
- the charging device 8 for example, a contact type charging device using a conductive or semiconductive charging roll, a charging brush, a charging film, a charging rubber blade, a charging tube, or the like is used. Further, per se known charging devices, such as a non-contact type roller charging device, and a scorotron charging device and a corotron charging device, each using corona discharge, and the like are also used.
- the exposure device 9 may be an optical instrument for exposure of the surface of the electrophotographic photoreceptor 7 , to rays such as a semiconductor laser ray, an LED ray, and a liquid crystal shutter ray according to an image data.
- the wavelength of the light source may be a wavelength in the range from the spectral sensitivity wavelengths of the electrophotographic photoreceptor.
- As the wavelengths of semiconductor lasers near infrared wavelengths that are oscillation wavelengths near 780 nm are predominant.
- the wavelength of the laser ray to be used is not limited to such a wavelength, and a laser having an oscillation wavelength of 600 nm range, or a laser having any oscillation wavelength in the range from 400 nm to 450 nm as a blue laser may be used.
- a planar light emission type laser light source capable of attaining a multi-beam output.
- a common developing device in which a developer is contacted or not contacted for forming an image
- a developing device 11 is not particularly limited as long as it has the above-described functions, and may be appropriately selected according to the intended use.
- Examples thereof include a known developing device in which the single-component or two-component developer is adhered to the electrophotographic photoreceptor 7 using a brush or a roller.
- the developing device using developing roller retaining developer on the surface thereof is preferable.
- the developer used in the developing device 11 may be a single-component developer formed of a toner alone or a two-component developer formed of a toner and a carrier. Further, the developer may be magnetic or non-magnetic. As the developer, known ones may be applied.
- a cleaning blade type device provided with the cleaning blade 131 is used.
- a fur brush cleaning type and a type of performing developing and cleaning at once may also be employed.
- Examples of the transfer device 40 include per se known transfer charging devices, such as a contact type transfer charging device using a belt, a roller, a film, a rubber blade, or the like, a scorotron transfer charging device utilizing corona discharge, and a corotron transfer charging device utilizing corona discharge.
- per se known transfer charging devices such as a contact type transfer charging device using a belt, a roller, a film, a rubber blade, or the like, a scorotron transfer charging device utilizing corona discharge, and a corotron transfer charging device utilizing corona discharge.
- the intermediate transfer member 50 a form of a belt (intermediate transfer belt) composed of polyimide, polyamideimide, polycarbonate, polyarylate, polyester, rubber, or the like, which is imparted with the semiconductivity, is used.
- the intermediate transfer member may also take the form of a drum, in addition to the form of a belt.
- FIG. 3 is a schematic structural view showing another example of the image forming apparatus according to the present exemplary embodiment.
- the image forming apparatus 120 shown in FIG. 3 is a tandem type full color image forming apparatus equipped with four process cartridges 300 .
- four process cartridges 300 are disposed parallel with each other on the intermediate transfer member 50 , and one electrophotographic photoreceptor may be used for one color.
- the image forming apparatus 120 has the same configuration as the image forming apparatus 100 , except that it is a tandem type.
- the image forming apparatus 100 is not limited to the configuration, and for example, it is in the periphery of the electrophotographic photoreceptor 7 . Further, it may be configured to provide a first erasing device for making the erasing with a cleaning brush easier by matching the polarity of the residual toner on the downstream side in the rotating direction of the electrophotographic photoreceptor 7 from the transfer device 40 and on the upstream side in the rotating direction of the electrophotographic photoreceptor from the cleaning device 13 , or to provide a second erasing device by erasing the charge of the surface of the electrophotographic photoreceptor 7 on the downstream side in the rotating direction of the electrophotographic photoreceptor from the cleaning device 13 and on the upstream side in the rotating direction of the electrophotographic photoreceptor from the charging device 8 .
- the image forming apparatus 100 is not limited to the configurations above, and for example, an image forming apparatus having a well-known configuration, in a direct transfer mode, in which a toner image formed in an electrophotographic photoreceptor 7 is directly transferred onto a recording medium, may be employed.
- the obtained coating liquid is coated on an aluminum substrate having a diameter of 30 mm, a length of 340 mm, and a thickness of 1 mm by a dip coating method, and dried to cure at 170° C. for 35 minutes, thereby obtaining an undercoat layer having a thickness of 16 m.
- A copolymerization type polycarbonate resin having the following structure as a binder resin
- 200 parts by weight of tetrahydrofuran as a solvent
- monochlorobenzene as a solvent
- a single layer type photosensitive layer having a film thickness of 26 ⁇ m is formed by coating the obtained coating liquid for forming a photosensitive layer on the undercoat layer formed on the aluminum substrate using a dip coating method, and drying at 140° C. for 1 hour.
- an electrophotographic photoreceptor is prepared.
- each electrophotographic photoreceptor is prepared.
- the charge potential is determined by measuring the potential of the surface of the electrophotographic photoreceptor before charging and exposing by a device in which a developer unit inside the HL2270DW is replaced by a potential probe.
- A The charge potential is decreased by 35 V or less.
Abstract
wherein X represents an oxygen atom or ═C(CN)2; R1, R2, R3, R4, R5, R6, and R7 each independently represent a hydrogen atom, a halogen atom, a linear or branched alkyl group, an alkoxy group, an aryl group, or an aralkyl group; R8, R9, and R10 each independently represent a hydrogen atom, a halogen atom, a linear or branched alkyl group, an aralkyl group, an aryl group, —R11—O—R12, or —R13—CO—O—R14; R11 represents a linear or branched alkylene group; R12 represents a linear or branched alkyl group; R13 represents a single bond or a linear or branched alkylene group; and R14 represents a linear or branched alkyl group, an aryl group, or an aralkyl group, provided that at least two or more groups of R8, R9, and R10 represent a group other than a hydrogen atom.
Description
Exemplary | |||||||||
Compound | X | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 |
1-1 | ═C(CN)2 | —H | —H | —H | —H | —H | —H | —H | —CH3 |
1-2 | ═C(CN)2 | —H | —H | —H | —H | —H | —H | —H | —CH3 |
1-3 | ═C(CN)2 | —H | —H | —H | —H | —H | —H | —H | —CH3 |
1-4 | ═C(CN)2 | —H | —H | —H | —H | —H | —H | —H | —CH3 |
1-5 | ═C(CN)2 | —H | —H | —H | —H | —H | —H | —H | —CH2OCH3 |
1-6 | ═C(CN)2 | —H | —H | —H | —H | —H | —H | —H | —CH(CH3)2 |
1-7 | ═C(CN)2 | —H | —H | —H | —H | —H | —H | —H | —CH(CH3)2 |
1-8 | ═C(CN)2 | —H | —H | —H | —H | —H | —H | —H | —CH3 |
1-9 | ═C(CN)2 | —H | —H | —H | —H | —H | —H | —H | -t-C4H9 |
1-10 | ═C(CN)2 | —H | —H | —H | —H | —H | —H | —H | -t-C4H9 |
1-11 | ═C(CN)2 | —H | —H | —H | —H | —H | —H | —H | —C(CH3)2CH2CH3 |
1-12 | ═C(CN)2 | —H | —H | —H | —H | —H | —H | —H |
|
1-13 | ═C(CN)2 | —H | —H | —H | —H | —H | —H | —H | -t-C4H9 |
1-14 | ═C(CN)2 | —H | —H | —H | —H | —H | —H | —H | -t-C4H9 |
1-15 | ═C(CN)2 | —H | —H | —H | —H | —H | —H | —H | -t-C4H9 |
1-16 | ═C(CN)2 | —H | —H | —H | —H | —H | —H | —H | -t-C4H9 |
1-17 | ═C(CN)2 | —H | —H | —H | —H | —H | —H | —H | -t-C4H9 |
1-18 | ═C(CN)2 | —H | —H | —H | —H | —H | —H | —H | -t-C4H9 |
1-19 | ═C(CN)2 | —H | —H | —H | —H | —H | —H | —H | -t-C4H9 |
1-20 | ═C(CN)2 | —H | —H | —H | —H | —H | —H | —H | -t-C4H9 |
1-21 | ═C(CN)2 | —H | Cl | —H | —H | Cl | —H | —H | —C(CH3)2CH2CH3 |
1-22 | ═C(CN)2 | —H | Cl | —H | —H | Cl | —H | —H | -n-C4H9 |
1-23 | ═C(CN)2 | —H | —CH3 | —H | —H | —H | —H | —H | —Cl |
1-24 | ═C(CN)2 | —H | —OCH3 | —H | —H | —H | —H | —H | -n-C9H19 |
1-25 | ═C(CN)2 | —OCH3 | —H | —H | —H | —H | —H | —H | —CH2OCH3 |
1-26 | ═O | —H | —H | —H | —H | —H | —H | —H | —CH3 |
1-27 | ═O | —H | —H | —H | —H | —H | —H | —H | —CH3 |
1-28 | ═O | —H | —H | —H | —H | —H | —H | —H | —CH3 |
1-29 | ═O | —H | —H | —H | —H | —H | —H | —H | —CH3 |
1-30 | ═O | —H | —H | —H | —H | —H | —H | —H | —CH2OCH3 |
1-31 | ═O | —H | —H | —H | —H | —H | —H | —H | —CH(CH3)2 |
1-32 | ═O | —H | —H | —H | —H | —H | —H | —H | —CH(CH3)2 |
1-33 | ═O | —H | —H | —H | —H | —H | —H | —H | —CH3 |
1-34 | ═O | —H | —H | —H | —H | —H | —H | —H | -t-C4H9 |
1-35 | ═O | —H | —H | —H | —H | —H | —H | —H | -t-C4H9 |
1-36 | ═O | —H | —H | —H | —H | —H | —H | —H | —C(CH3)2CH2CH3 |
1-37 | ═O | —H | —H | —H | —H | —H | —H | —H |
|
1-38 | ═O | —H | —H | —H | —H | —H | —H | —H | -t-C4H9 |
1-39 | ═O | —H | —H | —H | —H | —H | —H | —H | -t-C4H9 |
1-40 | ═O | —H | —H | —H | —H | —H | —H | —H | -t-C4H9 |
1-41 | ═O | —H | —H | —H | —H | —H | —H | —H | -t-C4H9 |
1-42 | ═O | —H | —H | —H | —H | —H | —H | —H | -t-C4H9 |
1-43 | ═O | —H | —H | —H | —H | —H | —H | —H | -t-C4H9 |
1-44 | ═O | —H | —H | —H | —H | —H | —H | —H | -t-C4H9 |
1-45 | ═O | —H | —H | —H | —H | —H | —H | —H | -t-C4H9 |
1-46 | ═O | —H | Cl | —H | —H | Cl | —H | —H | —C(CH3)2CH2CH3 |
1-47 | ═O | —H | Cl | —H | —H | Cl | —H | —H | -n-C4H9 |
1-48 | ═O | —H | —CH3 | —H | —H | —H | —H | —H | —Cl |
1-49 | ═O | —H | —OCH3 | —H | —H | —H | —H | —H | -n-C9H19 |
1-50 | ═O | —OCH3 | —H | —H | —H | —H | —H | —H | —CH2OCH3 |
Exemplary | position of | |||
Compound | R9 | R10 | R10 | |
1-1 | —CH3 | — | —H | |
1-2 | —CH3 | o-position | —CH3 | |
1-3 | —CH3 | m-position | —CH3 | |
1-4 | —C2H5 | — | —H | |
1-5 | -t-C4H9 | o-position | —CH2OCH3 | |
1-6 | —CH3 | o-position | —CH(CH3)2 | |
1-7 | -t-C4H9 | o-position | —CH(CH3)2 | |
1-8 | -n-C6H13 | — | —H | |
1-9 | —C2H5 | o-position | -t-C4H9 | |
1-10 | -t-C4H9 | — | —H | |
1-11 | —C(CH3)2CH2CH3 | — | —H | |
1-12 |
|
— | —H | |
1-13 | —CH2CH2CO2CH3 | o-position | -t-C4H9 | |
1-14 | —CH2CH2CO2CH2CH3 | o-position | -t-C4H9 | |
1-15 | —CH2CH2CO2CH2CH2CH2CH3 | o-position | -t-C4H9 | |
1-16 | —CH2CH2CO2-nC6H13 | o-position | -t-C4H9 | |
1-17 | —CH2CH2CO2-nC8H17 | o-position | -t-C4H9 | |
1-18 | —CH2CH2CO2-isoC8H17 | o-position | -t-C4H9 | |
1-19 |
|
o-position | -t-C4H9 | |
1-20 | —CO2-isoC8H17 | o-position | -t-C4H9 | |
1-21 | —C(CH3)2CH2CH3 | — | —H | |
1-22 | -n-C4H9 | — | —H | |
1-23 | —CO2-isoC8H17 | — | —H | |
1-24 | —CO2-isoC8H17 | — | —H | |
1-25 | —CO2-isoC8H17 | — | —H | |
1-26 | —CH3 | — | —H | |
1-27 | —CH3 | o-position | —CH3 | |
1-28 | —CH3 | m-position | —CH3 | |
1-29 | —C2H5 | — | —H | |
1-30 | -t-C4H9 | o-position | —CH2OCH3 | |
1-31 | —CH3 | o-position | —CH(CH3)2 | |
1-32 | -t-C4H9 | o-position | —CH(CH3)2 | |
1-33 | -n-C6H13 | — | —H | |
1-34 | —C2H5 | o-position | -t-C4H9 | |
1-35 | -t-C4H9 | — | —H | |
1-36 | —C(CH3)2CH2CH3 | — | —H | |
1-37 |
|
— | —H | |
1-38 | —CH2CH2CO2CH3 | o-position | -t-C4H9 | |
1-39 | —CH2CH2CO2CH2CH3 | o-position | -t-C4H9 | |
1-40 | —CH2CH2CO2CH2CH2CH2CH3 | o-position | -t-C4H9 | |
1-41 | —CH2CH2CO2-nC6H13 | o-position | -t-C4H9 | |
1-42 | —CH2CH2CO2-nC8H17 | o-position | -t-C4H9 | |
1-43 | —CH2CH2CO2-isoC8H17 | o-position | -t-C4H9 | |
1-44 |
|
o-position | -t-C4H9 | |
1-45 | —CO2-isoC8H17 | o-position | -t-C4H9 | |
1-46 | —C(CH3)2CH2CH3 | — | —H | |
1-47 | -n-C4H9 | — | —H | |
1-48 | —CO2-isoC8H17 | — | —H | |
1-49 | —CO2-isoC8H17 | — | —H | |
1-50 | —CO2-isoC8H17 | — | —H | |
TABLE 1 | |||||
Charge | Hole | Electron | |||
Undercoat | generating | transport | transport | ||
Example | Photoreceptor | layer | material | material | material |
Example 1 | Photoreceptor 1 | Included | HOGaPC | HT-7 | I-11 |
Example 2 | Photoreceptor 2 | None | HOGaPC | HT-7 | I-11 |
Example 3 | Photoreceptor 3 | Included | HOGaPC | HT-4 | I-12 |
Example 4 | Photoreceptor 4 | None | HOGaPC | HT-4 | I-12 |
Example 5 | Photoreceptor 5 | None | ClGaPC | HT-1 | I-11 |
Example 6 | Photoreceptor 6 | None | ClGaPC | HT-1 | I-12 |
Example 7 | |
None | ClGaPC | HT-7 | I-12 |
Example 8 | |
None | ClGaPC | HT-7 | I-36 |
Example 9 | |
None | X type | HT-1 | I-37 |
metal-free | |||||
phthalocyanine | |||||
Example 10 | Photoreceptor | None | X type | HT-1 | I-38 |
10 | metal-free | ||||
phthalocyanine | |||||
Comparative | Comparative | Included | HOGaPC | HT-1 | Comparative |
Example 1 | photoreceptor 1 | compound 1 | |||
Comparative | Comparative | None | HOGaPC | HT-1 | Comparative |
Example 2 | photoreceptor 2 | compound 2 | |||
Comparative | Comparative | None | HOGaPC | HT-4 | Comparative |
Example 3 | photoreceptor 3 | compound 3 | |||
Comparative | Comparative | None | ClGaPC | HT-1 | Comparative |
Example 4 | photoreceptor 4 | compound 4 | |||
Comparative | Comparative | None | X type | HT-1 | Comparative |
Example 5 | photoreceptor 5 | metal-free | compound 5 | ||
phthalocyanine | |||||
-
- HOGaPC: Hydroxygallium phthalocyanine (V type): V type hydroxygallium phthalocyanine pigment having diffraction peaks at the positions of at least 7.3°, 16.0°, 24.9°, and 28.0° by a Bragg angle (2θ±0.2°) in an X-ray diffraction spectrum obtained using CuKα characteristic X-ray (the maximum peak wavelength in a spectral absorption spectrum in a wavelength region of from 600 nm to 900 nm=820 nm, average particle diameter=0.12 μm, maximum particle diameter=0.2 μm, specific surface area value=60 m2/g)
- ClGaPC: Chlorogallium phthalocyanine: chlorogallium phthalocyanine pigment having diffraction peaks at the positions of at least 7.4°, 16.6°, 25.5°, and 28.3° by a Bragg angle (2θ±0.2°) in an X-ray diffraction spectrum obtained using CuKα characteristic X-ray (the maximum peak wavelength in a spectral absorption spectrum in a wavelength region of from 600 nm to 900 nm=780 nm, average particle diameter=0.15 μm, maximum particle diameter=0.2 μm, specific surface area value=56 m2/g)
- X type metal-free phthalocyanine: H2PC: metal-free phthalocyanine pigment (phthalocyanine having two hydrogen atoms coordinated at the center of a phthalocyanine skeleton)
-
- HT-7: an exemplary compound (HT-7) of the compound represented by the formula (B-1)
- HT-4: an exemplary compound (HT-4) of the compound represented by the formula (B-1)
- HT-1: an exemplary compound (HT-1) of the compound represented by the formula (B-2)
-
- 1-11: an exemplary compound (1-11) obtained in Synthesis Example 3
- 1-12: an exemplary compound (1-12) obtained in Synthesis Example 4
- 1-36: an exemplary compound (1-36) obtained in Synthesis Example 1
- 1-37: an exemplary compound (1-37) obtained in Synthesis Example 2
- Comparative compound 1: Comparative compound 1 obtained in Comparative Synthesis Example 1
- Comparative compound 2: Comparative compound 2 obtained in Comparative Synthesis Example 2
- Comparative compound 3: Comparative compound 3 obtained in Comparative Synthesis Example 3
- Comparative compound 4: Comparative compound 4 obtained in Comparative Synthesis Example 4
- Comparative compound 5: Comparative compound 5 obtained in Comparative Synthesis Example 5
TABLE 2 | |||||
Charge | |||||
potential | Evaluation | ||||
after | on charge | ||||
Initial | printing | maintenance | |||
Evaluation on | charge | 20000 | (decrease in | ||
Example | Photoreceptor | blur | potential | sheets | potential) |
Example 1 | Photoreceptor 1 | A | 600 V | 572 V | A (−28 V) |
Example 2 | Photoreceptor 2 | A | 605 V | 578 V | A (−27 V) |
Example 3 | Photoreceptor 3 | A | 601 V | 576 V | A (−25 V) |
Example 4 | Photoreceptor 4 | A | 603 V | 571 V | A (−32 V) |
Example 5 | Photoreceptor 5 | A | 596 V | 561 V | A (−35 V) |
Example 6 | Photoreceptor 6 | A | 600 V | 572 V | A (−28 V) |
Example 7 | Photoreceptor 7 | A | 602 V | 577 V | A (−25 V) |
Example 8 | Photoreceptor 8 | A | 599 V | 578 V | A (−21 V) |
Example 9 | Photoreceptor 9 | A | 606 V | 572 V | A (−34 V) |
Example 10 | Photoreceptor 10 | A | 603 V | 570 V | A (−33 V) |
Comparative | Comparative | C | 601 V | 543 V | C (−58 V) |
Example 1 | photoreceptor 1 | ||||
Comparative | Comparative | C | 595 V | 541 V | C (−54 V) |
Example 2 | photoreceptor 2 | ||||
Comparative | Comparative | B | 600 V | 557 V | B (−43 V) |
Example 3 | photoreceptor 3 | ||||
Comparative | Comparative | B | 600 V | 553 V | B (−47 V) |
Example 4 | photoreceptor 4 | ||||
Comparative | Comparative | B | 604 V | 559 V | B (−45 V) |
Example 5 | photoreceptor 5 | ||||
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